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Organic Chemistry: A Short Course 13th edition [Pehme köide]

(Central Connecticut State University), (Ohio State University), (Michigan State University), (The Ohio State University)
  • Formaat: Paperback / softback, kõrgus x laius x paksus: 25x215x274 mm, kaal: 1270 g
  • Ilmumisaeg: 03-Sep-2020
  • Kirjastus: Brooks/Cole
  • ISBN-10: 0357670892
  • ISBN-13: 9780357670897
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  • Formaat: Paperback / softback, kõrgus x laius x paksus: 25x215x274 mm, kaal: 1270 g
  • Ilmumisaeg: 03-Sep-2020
  • Kirjastus: Brooks/Cole
  • ISBN-10: 0357670892
  • ISBN-13: 9780357670897
Teised raamatud teemal:
Offering practical, real-life applications, coverage of basic concepts, and an engaging visual style, this proven book offers a writing style, approach, and selection of topics ideal for non-chemistry science majors. This edition offers an updated, dynamic art program (online, on CD, and in the text), new content to keep you current with developments in the organic chemistry field, and a revised lab manual.
Preface xvi
To the Student xxv
1 Bonding and Isomerism
1(12)
1.1 How Electrons Are Arranged In Atoms
2(1)
1.2 Ionic And Covalent Bonding
3(4)
1.2.a Ionic Compounds
4(1)
1.2.b The Covalent Bond
5(2)
1.3 Carbon And The Covalent Bond
7(1)
1.4 Carbon--Carbon Single Bonds
8(1)
1.5 Polar Covalent Bonds
9(2)
1.6 Multiple Covalent Bonds
11(1)
1.7 Valence
12(1)
1.8 Isomerism
13(1)
A CLOSER LOOK AT ...Green Chemistry
13(32)
1.9 Writing Structural Formulas
14(2)
1.10 Abbreviated Structural Formulas
16(2)
1.11 Formal Charge
18(2)
1.12 Resonance
20(1)
1.13 Arrow Formalism
21(2)
1.14 The Orbital View Of Bonding; The Sigma Bond
23(1)
1.15 Carbon Sp3 Hybrid Orbitals
24(1)
1.16 Tetrahedral Carbon; The Bonding In Methane
25(2)
1.17 Classification According To Molecular Framework
27(3)
1.17.a Acyclic Compounds
27(1)
1.17.b Carbocyclic Compounds
28(1)
1.17.c Heterocyclic Compounds
28(2)
1.18 Classification According To Functional Group
30(6)
Additional Problems
32(4)
2 Alkanes and Cycloalkanes; Conformational and Geometric Isomerism
36(9)
2.1 The Structures Of Alkanes
37(1)
2.2 Nomenclature Of Organic Compounds
38(1)
2.3 Iupac Rules For Naming Alkanes
39(2)
2.4 Alkyl And Halogen Substituents
41(2)
2.5 Use Of The Iupac Rules
43(1)
2.6 Sources Of Alkanes
44(1)
A CLOSER LOOK AT ...Natural Gas AA
2.7 Physical Properties Of Alkanes And Nonbonding Intermolecular Interactions
45(1)
A CLOSER LOOK AT ...Hydrogen Bonding
46(9)
2.8 Conformations Of Alkanes
47(2)
2.9 Cycloalkane Nomenclature And Conformation
49(5)
2.10 Cis-Trans Isomerism In Cycloalkanes
54(1)
A WORD ABOUT ...Isomers---Possible and Impossible
55(3)
2.11 Summary Of Isomerism
56(1)
2.12 Reactions Of Alkanes
56(2)
2.12.a Oxidation and Combustion; Alkanes as Fuels
57(1)
A WORD ABOUT ...Alternative Energy: The Benefits of Hydrogen
58(2)
2.12.b Halogenation of Alkanes
59(1)
A WORD ABOUT ...Methane, Marsh Gas, and Miller's Experiment
60(16)
2.13 The Free-Radical Chain Mechanism Of Halogenation
61(7)
Reaction Summary
63(1)
Mechanism Summary
63(1)
Additional Problems
63(5)
3 Alkenes and Alkynes
68(8)
3.1 Definition And Classification
69(1)
3.2 Nomenclature
70(3)
3.3 Some Facts About Double Bonds
73(1)
3.4 The Orbital Model Of A Double Bond; The Pi Bond
74(2)
A WORD ABOUT ...The Chemistry of Vision
76(22)
3.5 Cis-Trans Isomerism In Alkenes
76(2)
3.6 Addition And Substitution Reactions Compared
78(1)
3.7 Polar Addition Reactions
79(1)
3.7.a Addition of Halogens
79(1)
3.7.b Addition of Water (Hydration)
79(1)
3.7.c Addition of Acids
80(1)
3.8 Addition Of Unsymmetric Reagents To Unsymmetric Alkenes; Markovnikovs Rule
80(2)
3.9 Mechanism Of Electrophilic Addition To Alkenes
82(2)
3.10 Markovnikov's Rule Explained
84(2)
3.11 Reaction Equilibrium: What Makes A Reaction Go?
86(1)
3.12 Reaction Rates: How Fast Does A Reaction Go?
87(3)
3.13 Hydroboration Of Alkenes
90(1)
3.14 Addition Of Hydrogen
91(1)
3.15 Additions To Conjugated Systems
92(3)
3.15.a Electrophilic Additions to Conjugated Dienes
92(2)
3.15.b Cycloacldition to Conjugated Dienes: The Diels-Alder Reaction
94(1)
3.16 Free-Radical Additions; Polyethylene
95(1)
3.17 Oxiation Of Alkenes
96(2)
3.17.a Oxidation with Permanganate; a Chemical Test
97(1)
3.17.b Ozonolysis of Alkenes
97(1)
A WORD ABOUT ...Ethylene: Raw Material and Plant Hormone
98(4)
3.17.c Other Alkene Oxidations
99(1)
3.18 Some Facts About Triple Bonds
100(1)
3.19 The Orbital Model Of A Triple Bond
100(1)
3.20 Addition Reactions Of Alkynes
101(1)
A WORD ABOUT ...Petroleum, Gasoline, and Octane Number
102(3)
3.21 Acidity Of Alkynes
104(1)
A CLOSER LOOK AT ...Petroleum
105(23)
Reaction Summary
106(1)
Mechanism Summary
107(1)
Additional Problems
108(6)
4 Aromatic Compounds
114(14)
4.1 Some Facts About Benzene
115(1)
4.2 The Kekute Structure Of Benzene
116(1)
4.3 Resonance Model For Benzene
117(1)
4.4 Orbital Model For Benzene
117(1)
4.5 Symbols For Benzene
118(1)
4.6 Nomenclature Of Aromatic Compounds
118(3)
4.7 The Resonance Energy Of Benzene
121(1)
4.8 Electrophilic Aromatic Substitution
122(1)
4.9 The Mechanism Of Electrophilic Aromatic Substitution
123(5)
4.9.a Halogenation
125(1)
4.9.b Nitration
126(1)
4.9.c Sulfonation
126(1)
4.9.d Alkylation and Acylation
127(1)
A WORD ABOUT ...Vitamin E: Tocopherols and Tocotrienols
128(8)
4.10 Ring-Activating And Ring-Deactivating Substituents
128(1)
4.11 Ortho, Para-Directing And Meta-Directing Groups
129(5)
4.11.a Ortho, Para-Directing Groups
130(2)
4.11.b Meta-Directing Groups
132(2)
4.11.c Substituent Effects on Reactivity
134(1)
4.12 The Importance Of Directing Effects In Synthesis
134(1)
4.13 Polycyclic Aromatic Hydrocarbons
135(1)
A WORD ABOUT ...Polycyclic Aromatic Hydrocarbons and Cancer
136(1)
A CLOSER LOOK AT ...Polycyclic Aromatic Hydrocarbons
137(1)
A WORD ABOUT ...C60, an Aromatic Sphere: The Fullerenes
138(22)
Reaction Summary
140(1)
Mechanism Summary
141(1)
Additional Problems
141(6)
5 Stereoisomerism
147(13)
5.1 Chirality And Enantiomers
148(1)
5.2 Stereogenic Centers; The Stereogenic Carbon Atom
149(4)
5.3 Configuration And The R-S Convention
153(4)
5.4 The E-Z Convention For Cis-Trans Isomers
157(1)
5.5 Polarized Light And Optical Activity
158(2)
A WORD ABOUT ...Pasteur's Experiments and the van't Hoff-LeBel Explanation
160(12)
5.6 Properties Of Enantiomers
162(1)
5.7 Fischer Projection Formulas
163(2)
5.8 Compounds With More Than One Stereogenic Center; Diastereomers
165(2)
5.9 Meso Compounds; The Stereoisomers Of Tartaric Acid
167(2)
5.10 Stereochemistry: A Recap Of Definitions
169(1)
5.11 Stereochemistry And Chemical Reactions
170(2)
A WORD ABOUT ...Enantiomers and Biological Activity
172(2)
5.12 Resolution Of A Racemic Mixture
173(1)
A CLOSER LOOK AT ...Thalidomide
174(1)
A WORD ABOUT ...Green Chemistry: L-DOPA
175(18)
Additional Problems
176(6)
6 Organic Halogen Compounds; Substitution and Elimination Reactions
182(11)
6.1 Nucleophilic Substitution
183(1)
6.2 Examples Of Nucleophilic Substitutions
183(4)
6.3 Nucleophilic Substitution Mechanisms
187(1)
6.4 The Sn2 Mechanism
187(3)
6.5 The Sn1 Mechanism
190(2)
6.6 The Sn1 And Sn2 Mechanisms Compared
192(1)
A WORD ABOUT ...SN2 Reactions in Nature: Biological Methylations
193(7)
6.7 Dehydrohalogenation, An Elimination Reaction; The E2 And E1 Mechanisms
195(1)
6.8 Substitution And Elimination In Competition
196(3)
6.8.a Tertiary Halides
196(1)
6.8.b Primary Halides
197(1)
6.8.c Secondary Halides
197(2)
6.9 Polyhalogenated Aliphatic Compounds
199(1)
A WORD ABOUT ...CFCs, the Ozone Layer, and Trade-Offs
200(1)
A WORD ABOUT ...Halogenated Organic Compounds from the Sea
201(7)
Reaction Summary
202(1)
Mechanism Summary
202(1)
Additional Problems
203(3)
7 Alcohols, Phenols, and Thiols
206(2)
7.1 Nomenclature Of Alcohols
207(1)
A WORD ABOUT ...Industrial Alcohols
208(14)
7.2 Classification Of Alcohols
209(1)
7.3 Nomenclature Of Phenols
209(1)
7.4 Hydrogen Bonding In Alcohols And Phenols
210(1)
7.5 Acidity And Basicity Reviewed
211(2)
7.6 The Acidity Of Alcohols And Phenols
213(3)
7.7 The Basicity Of Alcohols And Phenols
216(1)
7.8 Dehydration Of Alcohols To Alkenes
216(2)
7.9 The Reaction Of Alcohols With Hydrogen Halides
218(1)
7.10 Other Ways To Prepare Alkyl Halides From Alcohols
219(1)
7.11 A Comparison Of Alcohols And Phenols
220(1)
7.12 Oxidation Of Alcohols To Aldehydes, Ketones, And Carboxylic Acids
220(2)
A WORD ABOUT ...Biologically Important Alcohols and Phenols
222(3)
7.13 Alcohols With More Than One Hydroxyl Group
223(1)
7.14 Aromatic Substitution In Phenols
224(1)
A WORD ABOUT ...Quinones and the Bombardier Beetle
225(3)
7.15 Oxidation Of Phenols
225(1)
7.16 Phenols As Antioxidants
226(1)
7.17 Thiols, The Sulfur Analogs Of Alcohols And Phenols
227(1)
A WORD ABOUT ...Hair---Curly or Straight
228(13)
Reaction Summary
229(1)
Additional Problems
230(4)
8 Ethers and Epoxides
234(7)
8.1 Nomenclature Of Ethers
235(1)
8.2 Physical Properties Of Ethers
236(1)
8.3 Ethers As Solvents
237(1)
8.4 The Grignard Reagent; An Organometallic Compound
237(3)
8.5 Preparation Of Ethers
240(1)
A CLOSER LOOK AT ...MTBE
241(2)
8.6 Cleavage Of Ethers
242(1)
A WORD ABOUT ...Ether and Anesthesia
243(2)
8.7 Epoxides (Oxiranes)
244(1)
A WORD ABOUT ...The Gypsy Moth's Epoxide
245(29)
8.8 Reactions Of Epoxides
245(2)
8.9 Cyclic Ethers
247(6)
Reaction Summary
249(1)
Additional Problems
250(3)
9 Aldehydes and Ketones
253(21)
9.1 Nomenclature Of Aldehydes And Ketones
254(1)
9.2 Some Common Aldehydes And Ketones
255(2)
9.3 Synthesis Of Aldehydes And Ketones
257(1)
9.4 Aldehydes And Ketones In Nature
258(1)
9.5 The Carbonyl Group
259(1)
9.6 Nucleophilic Addition To Carbonyl Groups: An Overview
260(1)
9.7 Addition Of Alcohols: Formation Of Hemiacetals And Acetals
261(3)
9.8 Addition Of Water; Hydration Of Aldehydes And Ketones
264(1)
9.9 Addition Of Grignard Reagents And Acetylides
265(3)
9.10 Addition Of Hydrogen Cyanide; Cyanohydrins
268(1)
9.11 Addition Of Nitrogen Nucleophiles
269(1)
9.12 Reduction Of Carbonyl Compounds
270(1)
9.13 Oxidation Of Carbonyl Compounds
271(1)
9.14 Keto-Enol Tautomerism
272(2)
A WORD ABOUT ...Tautomerism and Photochromism
274(5)
9.15 Acidity Of α-Hydrogens; The Enolate Anion
275(1)
9.16 Deuterium Exchange In Carbonyl Compounds
276(1)
9.17 The Aldol Condensation
277(1)
9.18 The Mixed Aldol Condensation
278(1)
A WORD ABOUT ...Water Treatment and the Chemistry of Enols/Enolates
279(20)
9.19 Commercial Syntheses Via The Aldol Condensation
280(7)
Reaction Summary
281(1)
Mechanism Summary
282(1)
Additional Problems
282(5)
10 Carboxylic Acids and Their Derivatives
287(12)
10.1 Nomenclature Of Acids
288(3)
10.2 Physical Properties Of Acids
291(1)
10.3 Acidity And Acidity Constants
292(1)
10.4 What Makes Carboxylic Acids Acidic?
293(2)
10.5 Effect Of Structure On Acidity; The Inductive Effect Revisited
295(1)
10.6 Conversion Of Acids To Salts
296(1)
10.7 Preparation Of Acids
296(3)
10.7.a Oxidation of Primary Alcohols and Aldehydes
296(1)
10.7.b Oxidation of Aromatic Side Chains
297(1)
10.7.c Reaction of Grignard Reagents with Carbon Dioxide
298(1)
10.7.d Hydrolysis of Cyanides (Nitriles)
298(1)
A WORD ABOUT ...Green Chemistry and Ibuprofen: A Case Study
299(13)
10.8 Carboxylic Acid Derivatives
300(1)
10.9 Esters
301(1)
10.10 Preparation Of Esters; Fischer Esterification
302(1)
10.11 The Mechanism Of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution
302(2)
10.12 Lactones
304(1)
10.13 Saponification Of Esters
305(1)
10.14 Ammonolysis Of Esters
306(1)
10.15 Reaction Of Esters With Grignard Reagents
307(1)
10.16 Reduction Of Esters
307(1)
10.17 The Need For Activated Acyl Compounds
308(1)
10.18 Acyl Halides
309(1)
10.19 Acid Anhydrides
310(2)
A WORD ABOUT ...Thioesters, Nature's Acyl-Activating Groups
312(29)
10.20 Amides
313(2)
10.21 A Summary Of Carboxylic Acid Derivatives
315(2)
10.22 The α-Hydrogen Of Esters; The Claisen Condensation
317(10)
Reaction Summary
320(1)
Mechanism Summary
321(1)
Additional Problems
321(6)
11 Amines and Related Nitrogen Compounds
327(14)
11.1 Classification And Structure Of Amines
328(1)
11.2 Nomenclature Of Amines
329(1)
11.3 Physical Properties And Intermolecular Interactions Of Amines
330(1)
11.4 Preparation Of Amines; Alkylation Of Ammonia And Amines
331(2)
11.5 Preparation Of Amines; Reduction Of Nitrogen Compounds
333(2)
11.6 The Basicity Of Amines
335(3)
11.7 Comparison Of The Basicity And Acidity Of Amines And Amides
338(2)
11.8 Reaction Of Amines With Strong Acids; Amine Salts
340(1)
A WORD ABOUT ...Alkaloids and the Dart-Poison Frogs
341(27)
11.9 Chiral Amines As Resolving Agents
342(1)
11.10 Acylation Of Amines With Acid Derivatives
343(1)
11.11 Quaternary Ammonium Compounds
344(1)
11.12 Aromatic Diazonium Compounds
345(3)
11.13 Diazo Coupling; Azo Dyes
348(8)
Reaction Summary
350(1)
Mechanism Summary
351(1)
Additional Problems
351(5)
12 Spectroscopy and Structure Determination
356(12)
12.1 Principles Of Spectroscopy
357(2)
12.2 Nuclear Magnetic Resonance Spectroscopy
359(9)
12.2.a Measuring an NMR Spectrum
359(1)
12.2.b Chemical Shifts and Peak Areas
360(4)
12.2.c Spin-Spin Splitting
364(4)
A WORD ABOUT ...NMR in Biology and Medicine
368(13)
12.3 13C Nmr Spectroscopy
368(3)
12.4 Infrared Spectroscopy
371(4)
12.5 Visible And Ultraviolet Spectroscopy
375(2)
12.6 Mass Spectrometry
377(4)
A CLOSER LOOK AT ...Mass Spectrometry and Carbon Dating
381(21)
Additional Problems
382(8)
13 Heterocyclic Compounds
390(12)
13.1 Pyridine: Bonding And Basicity
391(1)
13.2 Substitution In Pyridine
392(3)
13.3 Other Six-Membered Heterocycles
395(3)
13.4 Five-Membered Heterocycles: Furan, Pyrrole, And Thiophene
398(2)
13.5 Electrophilic Substitution In Furan, Pyrrole, And Thiophene
400(1)
13.6 Other Five-Membered Heterocycles: Azoles
401(1)
A WORD ABOUT ...Porphyrins: What Makes Blood Red and Grass Green?
402(3)
13.7 Fused-Ring Five-Membered Heterocycles: Indoles And Purines
403(2)
A WORD ABOUT ...Morphine and Other Nitrogen-Containing Drugs
405(16)
Reaction Summary
407(1)
Mechanism Summary
408(1)
Additional Problems
408(3)
14 Synthetic Polymers
411(10)
14.1 Classification Of Polymers
412(1)
14.2 Free-Radical Chain-Growth Polymerization
412(6)
14.3 Cationic Chain-Growth Polymerization
418(1)
14.4 Anionic Chain-Growth Polymerization
419(1)
14.5 Stereoregular Polymers; Ziegler-Natta Polymerization
420(1)
A WORD ABOUT ...Polyacetylene and Conducting Polymers
421(5)
14.6 Diene Polymers: Natural And Synthetic Rubber
422(2)
14.7 Copolymers
424(1)
14.8 Step-Growth Polymerization: Dacron And Nylon
425(1)
A WORD ABOUT ...Degradable Polymers
426(1)
A WORD ABOUT ...Aramids, the Latest in Polyamides
427(2)
A CLOSER LOOK AT ...Nylon
429(18)
14.9 Polyurethanes And Other Step-Growth Polymers
429(9)
Reaction Summary
433(1)
Mechanism Summary
434(1)
Additional Problems
435(3)
15 Lipids and Detergents
438(9)
15.1 Fats And Oils; Triesters Of Glycerol
439(3)
15.2 Hydrogenation Of Vegetable Oils
442(1)
15.3 Saponification Of Fats And Oils; Soap
443(1)
15.4 How Do Soaps Work?
444(1)
15.5 Synthetic Detergents (Syndets)
445(2)
A WORD ABOUT ...Commercial Detergents
447(3)
15.6 Phospholipids
449(1)
A WORD ABOUT ...Prostaglandins, Aspirin, and Pain
450(29)
15.7 Prostaglandins, Leukotrienes, And Lipoxins
451(1)
15.8 Waxes
452(1)
15.9 Terpenes And Steroids
452(8)
Reaction Summary
457(1)
Additional Problems
457(3)
16 Carbohydrates
460(19)
16.1 Definitions And Classification
461(1)
16.2 Monosaccharides
461(1)
16.3 Chirality In Monosaccharides; Fischer Projection Formulas And D,L-Sugars
462(4)
16.4 The Cyclic Hemiacetal Structures Of Monosaccharides
466(2)
16.5 Anomeric Carbons; Mutarotation
468(1)
16.6 Pyranose And Furanose Structures
469(1)
16.7 Conformations Of Pyranoses
470(1)
16.8 Esters And Ethers From Monosaccharides
471(1)
16.9 Reduction Of Monosaccharides
472(1)
16.10 Oxidation Of Monosaccharides
472(1)
16.11 Formation Of Glycosides From Monosaccharides
473(2)
16.12 Disaccharides
475(4)
16.12.a Maltose
475(1)
16.12.b Cellobiose
476(1)
16.12.c Lactose
476(1)
16.12.d Sucrose
477(2)
A WORD ABOUT ...Sweetness and Sweeteners
479(3)
16.13 Polysaccharides
480(2)
16.13.a Starch and Glycogen
480(1)
16.13.b Cellulose
481(1)
A WORD ABOUT ...Fat Substitutes from Carbohydrates
482(2)
16.13.c Other Polysaccharides
483(1)
A WORD ABOUT ...Green Chemistry: Alternative Uses for Carbohydrates
484(19)
16.14 Sugar Phosphates
485(1)
16.15 Deoxy Sugars
485(1)
16.16 Amino Sugars
485(1)
16.17 Ascorbic Acid (Vitamin C)
486(6)
Reaction Summary
487(1)
Additional Problems
488(4)
17 Amino Acids, Peptides, and Proteins
492(11)
17.1 Naturally Occurring Amino Acids
493(2)
17.2 The Acid--Base Properties Of Amino Acids
495(3)
17.3 The Acid--Base Properties Of Amino Acids With More Than One Acidic Or Basic Group
498(2)
17.4 Electrophoresis
500(1)
17.5 Reactions Of Amino Acids
500(1)
17.6 The Ninhydrin Reaction
501(1)
17.7 Peptides
502(1)
A WORD ABOUT ...Some Naturally Occurring Peptides
503(7)
17.8 The Disulfide Bond
504(1)
17.9 Proteins
505(1)
17.10 The Primary Structure Of Proteins
505(4)
17.10.a Amino Acid Analysis
505(1)
17.10.b Sequence Determination
506(2)
17.10.c Cleavage of Selected Peptide Bonds
508(1)
17.11 The Logic Of Sequence Determination
509(1)
A WORD ABOUT ...Protein Sequencing and Evolution
510(10)
17.12 Peptide Synthesis
511(4)
17.13 Secondary Structure Of Proteins
515(2)
17.13.a Geometry of the Peptide Bond
515(1)
17.13.b Hydrogen Bonding
515(1)
17.13.c The a Helix and the Pleated Sheet
516(1)
17.14 Tertiary Structure: Fibrous And Globular Proteins
517(2)
17.15 Quaternary Protein Structure
519(1)
A CLOSER LOOK AT ...Nobel Laureates and Protein Chemistry
520(14)
Reaction Summary
521(1)
Additional Problems
522(5)
18 Nucleotides and Nucleic Acids
527(7)
18.1 The General Structure Of Nucleic Acids
528(1)
18.2 Components Of Deoxyribonucleic Acid (Dna)
528(1)
18.3 Nucleosides
529(2)
18.4 Nucleotides
531(1)
18.5 The Primary Structure Of Dna
532(1)
18.6 Sequencing Nucleic Acids
533(1)
A WORD ABOUT ...DNA and Crime
534(5)
18.7 Laboratory Synthesis Of Nucleic Acids
534(1)
18.8 Secondary Dna Structure; The Double Helix
535(2)
18.9 Dna Replication
537(2)
A CLOSER LOOK AT ...The Polymerase Chain Reaction (PCR)
539(3)
18.10 Ribonucleic Acids; Rna
539(2)
18.11 The Genetic Code And Protein Biosynthesis
541(1)
A WORD ABOUT ...The Human Genome
542(2)
A WORD ABOUT ...Nucleic Acids and Viruses
544(9)
18.12 Other Biologically Important Nucleotides
546(7)
Reaction Summary
549(1)
Additional Problems
549(4)
Appendix 553(3)
Index/Glossary 556